Can Oliver Queen ever truly be happy? That's a question that ran through the first five years of Arrow and will be central to the show's new season.

Fans of The CW superhero series have grown accustomed to the character's dour personality and guilt-ridden conscience. No that you could blame him: Despite the many people he has saved, Oliver (Stephen Amell) has, after all, seen the deaths of his father, mother, best friend and ex-girlfriend (among many, many others). But now that the show has come full circle with his origin story — by way of five years' worth of flashbacks to his time shipwrecked on the island of Lian Yu and his journey from spoiled playboy to selfless superhero — the Green Arrow may actually crack a smile or two.

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"Oliver by design was created and written as a character who was always being held back by his past, whether it be his family, his father's death or his time on Lian Yu and Hong Kong and Russia down to all the mistakes he's made in the first 100 episodes of the show," executive producer Marc Guggenheim tells SYFY. "So the goal coming into Season 6 is to really write Oliver from a different perspective. He's made peace with his demons [and is] moving forward not just with a sense of being free from the bonds of the past, but also with the benefit of knowledge and maturity."

Of course, before he can get there, there is the matter of settling up on last May's explosive cliffhanger. Prometheus/Adrian Chase (Josh Segarra), perhaps the show's most formidable villain to date, capped off his season-long torment of Oliver by taking his own life and triggering a massive explosion on Lian Yu — where every member of Team Arrow was desperately trying to escape. Oliver had saved his kidnapped son, William (Jack Moore), from Prometheus, but expect life-changing consequences when the dust (literally) settles on the island. For a show that's produced its share of shocking moments, Arrow had never finished a season with such a spectacular lack of resolution.

"Going into Season 5, knowing that we were going to have our 100th episode, we started making a list of all the things that we'd done on the show and didn't want to repeat and then also things that we'd never done on the show before," Guggenheim recalls. "And one of the things that occurred to us was that we'd never done a proper cliffhanger to end the season. As we got deeper and deeper into plotting out the whole Prometheus plot, it made sense to us. It came together organically, which is really how we try to do things."

That's a perfect illustration of how the producers start the season with a specific story in mind, but take a nimble approach to plotting. "It's generally been more a process of refinement than it is change," Guggenheim says. "We never want to lose an awesome idea just because it wasn't part of our original plan. The audience doesn't know what our original plan was, they only know what's cool. We always give ourselves the option of throwing everything out that we planned and going with a last-minute inspiration if it fits the definition of something we want to do."

For example, in Season 2 the goal in the writers room had always been for Oliver to stop using lethal force in his crime-fighting crusade to save Starling City, and that Deathstroke would be the season's central adversary. "We knew that we wanted to get Oliver to a point where he had every reason in the world to kill Deathstroke and would choose not to," Guggenheim says. "What we didn't have was that reason to kill Deathstroke. The idea that he was going to kill [Oliver's mother] Moira came very late in the game. We as writers give ourselves permission to change things."

The cliffhanger has meant that the producers and cast have been far less generous with teasers for the new episodes. What we do know is that Oliver will step up in his roles as a father to William and as a mentor to Green Arrow's allies; Katie Cassidy returns to the cast full time, but as Black Siren, the Earth-2 version of her original character, the deceased Laurel Lance; Kirk Acevedo (Fringe) and Michael Emerson (Person of Interest) join the ensemble as major antagonists for Team Arrow; and Oliver's secret identity might not be a secret much longer.

And while this season hasn't even premiered, plans are already afoot for next year. "The way it tends to work with Arrow is that as we get into the back half of the year, past the midseason premiere, we're still breaking the current season, but in the writers room our minds will wander to the next season," Guggenheim says. "That has happened even earlier in our process than as is typical. We actually already have ideas for things we want to do Season 7. We're way ahead of where we typically are with those ideas."